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Syllabus and Schedule of Organic Chemistry II for Exam | CHEM 226, Exams of Organic Chemistry

Lake Superior State University (LSSU)Organic Chemistry
Prof. Robert M. Werner

Material Type: Exam; Professor: Werner; Class: Organic Chemistry II; Subject: Chemistry; University: Lake Superior State University; Term: Spring 2004;

Typology: Exams

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CHEM 226 Spring 2004 Organic Chemistry II
Lecture MWF 9-9:50 AM, Rm. 205 Crawford Hall
Lab Tue. (section A) 9-12 AM , Tue. (section B) 2-5 PM, or Wed.. (section C) 2-5PM , Rm. 335 Crawford
Dr. M. Werner office: CRW 314, phone: 635-2281 email: mwerner@lssu.edu
Office hours: Mon. and Wed. 10-12 AM or by appointment
State Council of State Science Supervisors:
http://www.csss-science.org/safety.shtml
http://www.csss-science.org/downloads/scisafe.pdf
Required Text: Organic Chemistry, McMurry, 5th ed.
*Week of: Topics McMurry Chapter
Jan. 12 Organic review Chapter 16 pg. 645-652
14 Alcohols and Phenols Chapter 17
16 Rxns. of alcohols and phenols
Jan. 19 Ethers and Epoxides, Thiols and Sulfides Chapter 18
21 Aldehydes and Ketones Chapter 19
23 Nucleophilic addition
Jan. 26 Nucleophilic addition
28 , unsaturated additions
30 Wittig Reaction
Feb. 2 Exam #1
4 Spectroscopic methods, MW, MS, IR Chapter 13
6 Spectroscopic methods NMR
Feb. 9 Spectroscopic methods, NMR
11 Conjugated Dienes, UV spectroscopy, Chapter 14
13 Aromatic Compounds Chapter 15
Feb. 16 Chemistry of Benzene
18 Electrophilic Aromatic Substitution Chapter 16
20 Electrophilic Aromatic Substitution
Feb. 23 NO CLASS
25 Reactions of Aromatics
27 Exam #2 (Spectroscopy Problems Due)
Mar. 1-5 Spring Break – NO CLASS
Mar. 8 Carboxylic acids Chapter 20
10 Acidity
12 Carboxylic Acid Derivatives Chapter 21
Mar. 15 Nucleophilic Acyl Sub. Rxns.
17 Esters and Amides
19 Carbonyl -Sub. Rxns. Chapter 22
Mar. 22 Enolates
24 Enolates
26 Carbonyl Condensation Reactions Chapter 23
Mar. 29 Claisen and Michael Rxns.
31 Exam #3
Apr 2 Carbohydrates Chapter 25
Apr. 5 Rxns. of Monosaccharides
7 Amines, Heterocycles Chapter 24
9 Special Lecture – View Poster Projects
Apr. 12 Rxns of Amines
14 Rxns of Amines
16 Amino Acids, Peptides, Proteins Chapter 26
Apr. 19 Proteins
21 Exam #4
23 Review
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CHEM 226 Spring 2004 Organic Chemistry II

Lecture MWF 9-9:50 AM, Rm. 205 Crawford Hall Lab Tue. (section A) 9-12 AM , Tue. (section B) 2-5 PM, or Wed.. (section C) 2-5PM , Rm. 335 Crawford

Dr. M. Werner office: CRW 314, phone: 635-2281 email: mwerner@lssu.edu

Office hours: Mon. and Wed. 10-12 AM or by appointment State Council of State Science Supervisors: http://www.csss-science.org/safety.shtml http://www.csss-science.org/downloads/scisafe.pdf

Required Text: Organic Chemistry, McMurry, 5th^ ed.

*Week of: Topics McMurry Chapter Jan. 12 Organic review Chapter 16 pg. 645- 14 Alcohols and Phenols Chapter 17 16 Rxns. of alcohols and phenols Jan. 19 Ethers and Epoxides, Thiols and Sulfides Chapter 18 21 Aldehydes and Ketones Chapter 19 23 Nucleophilic addition Jan. 26 Nucleophilic addition 28 , unsaturated additions 30 Wittig Reaction Feb. 2 Exam # 4 Spectroscopic methods, MW, MS, IR Chapter 13 6 Spectroscopic methods NMR Feb. 9 Spectroscopic methods, NMR 11 Conjugated Dienes, UV spectroscopy, Chapter 14 13 Aromatic Compounds Chapter 15 Feb. 16 Chemistry of Benzene 18 Electrophilic Aromatic Substitution Chapter 16 20 Electrophilic Aromatic Substitution Feb. 23 NO CLASS 25 Reactions of Aromatics 27 Exam #2 (Spectroscopy Problems Due) Mar. 1-5 Spring Break – NO CLASS Mar. 8 Carboxylic acids Chapter 20 10 Acidity 12 Carboxylic Acid Derivatives Chapter 21 Mar. 15 Nucleophilic Acyl Sub. Rxns. 17 Esters and Amides 19 Carbonyl -Sub. Rxns. Chapter 22 Mar. 22 Enolates 24 Enolates 26 Carbonyl Condensation Reactions Chapter 23 Mar. 29 Claisen and Michael Rxns. 31 Exam # Apr 2 Carbohydrates Chapter 25 Apr. 5 Rxns. of Monosaccharides 7 Amines, Heterocycles Chapter 24 9 Special Lecture – View Poster Projects Apr. 12 Rxns of Amines 14 Rxns of Amines 16 Amino Acids, Peptides, Proteins Chapter 26 Apr. 19 Proteins 21 Exam # 23 Review

Apr. 28 Comprehensive ACS Final Exam Wednesday Apr. 28 7:30 AM *This is a tentative schedule and may be modified as I deem necessary. Objective: My aim is to introduce you to the concepts necessary for understanding organic chemistry. I realize that most of you have varied career plans, but if I can excite just one of you enough to want to take another chemistry course or become involved in chemical research or applications, I have succeeded in my objective. Format : This course will follow the text, however the order of chapters has been rearranged. I realize this may be an inconvenience, but my lecture notes will present the material in a more cohesive and logical fashion than the book. Lectures will be 50 min containing copious problem solving examples. Your active participation in the lecture is appreciated and encouraged, however, if time is a limitation, I may ask you to see me after lecture. It is vital that you read the material prior to coming to class. Do not bring your text to class. Why? Focus your attention on the lecture notes and the discussion going on in class. Don’t bother trying to flip through the text to see how my presentation differs. I will extensively utilize assorted visual aids during the lectures as learning aids, most not from the book. BE PREPARED TO TAKE YOUR OWN NOTES! I suggest a loose-leaf notebook for taking your notes. Course Website: We will be using WebCT, the university’s internet utility, to post emails, old exams, helpful websites, and assignments for the class. The handouts for the laboratory will be posted here and you will be expected to print these off before you come to that week’s lab. The first week of class, I will distribute your username and password and will give you 10 extra credit points if you log on by Friday Jan. 16th, and email me using the WebCT email tool on the CH226 Home Page. You will find these material at the following website for the LSSU WebCT server: http://webcta.lssu.edu Once you log on to this website, you will be asked for a username and password. I will give these to you during the first lecture. You will then be asked to add the course you are interested in. You should have access to add Organic Chemistry II (under the Chemistry Section on WebCT). Follow the directions. Once logged on to the site you should change your password. The WebCT home page for Organic Chemistry II will have links on the home page. Assigned Problems: At the beginning of lecture, I may assign problems from the text or the lab manual. These problems will not be turned in for a grade but may appear in similar form on exams. The first several weeks of this course will involve limited review of the previous semester’s material. I suggest that you at least look over your notes from Organic I. Study Habits:

  1. Read the material before coming to lecture, preferably the night before, not in the car on your way to lecture.
  2. Recopy your notes after the lecture, preferably before the next lecture. When doing this, have the text open and expand your notes with points I may have glanced over or that you find of interest. Try to keep your notes in an outline format. Chemistry is a logical science, your notes should reflect that. Why recopy your notes? By recopying your notes you have actually written out the material 2 times. This is the best way I have found to learn material. In addition, you now have an excellent set of notes from which to study for exams.
  3. Do Problems. Lots of them, preferably just after rewriting your notes. I suggest trying all of the problems yourself without looking at the answers. Then go back and convince yourself that you actually understand a particular problem. Do not be passive when doing problems. Seek human help before resorting to the study guide.
  4. Study groups are fine but be cautious. Don’t rely on some one else to do the problems that you should be doing. Instead, I suggest that you talk about chemistry with your classmates and quiz each other with questions of your own origin.
  5. By scheduling approx. 2 hr every night after lecture (that’s 6 hr/week) to do the above things, you will undoubtedly realize significant results. Attendance/Absences : This course will cover material quickly and my notes often will stray from the book; it is very important that you attend class every period. No formal record of lecture attendance is

for determination of reasonable academic accommodations. OSASS is located in the KJS Library, Office 144, Ext. 7559. *I retain the right to change this syllabus, as I deem necessary at any time during the semester.

CHEM 226 Spring 2004 Organic Chemistry II Laboratory

Lab: Tue. (section A) 9-12 AM, Tue. (section B) 2-5 PM, or Wed.. (section C) 2-5 PM, Rm. 335 Crawford Dr. M. Werner office: CRW 314, phone: 635- 2281 email: mwerner@lssu.edu Required Lab text : Multiscale (or Microscale) Operational Organic Chemistry, Lehman, 1st^ ed. 2002 Required Lab Extras : Lab Notebook with gridded carbon copy pages (available in the book store), Safety goggles or glasses, and a lab apron or coat (optional). The purpose of the laboratory in CHEM 226 is to acquaint you with laboratory techniques encountered in organic research and to give you practical experience in performing organic experiments. The experiments were selected based on the techniques used, the molecules assayed and to some extent application to lecture material. You will need to purchase a lab notebook with gridded duplicate pages. Goggles or safety glasses and lab apron are required and your must have them prior to the beginning of the lab. Both notebooks and safety goggles are available at the book store. Other materials needed: several permanent marking pens (Sharpies are the best) Week of: Experiment Name pts Exp. # Jan. 12 No Lab - None Jan. 19 ☺ Testing Hypothesis, Gaseous Alkene 25 Minilab 4 + Jan. 26 Alcohols, pH, and Esters 25 Minilab 25,36, Feb. 2 Prep. of fluorescent dye 25 Minilab 26 Feb. 9 ☺ Haloform Oxidation 25 40 Feb. 16 Electronic Effect of p-iodo Substituient 25 41 Feb. 23 ☺ Preparation of DEET 25 43 Mar. 1 Spring Break - None Mar. 8 Rxn. Of Phthalimide 25 46 Mar. 15 ☺ Unknown D-Hexose 25 50 Mar. 22 Synth.of 2-Acetylcyclohexanone 50 45 (WebCT) Mar. 29 ☺ Synth.of 2-Acetylcyclohexanone 45 (Web CT) Apr. 5 Qualitative Organic Analysis 50 Part IV Apr. 12 ☺ Qualitative Organic Analysis Part IV Apr. 19 Qualitative Organic Analysis Part IV Apr. 26 Finals Week - None Note: The symbol ☺ weeks that a quiz will be given on lecture material. The weeks of Mar. 22- March 29 involve a multistep synthesis and may require additional time. The weeks of Apr. 5 – Apr. 19 involve the identification of an unknown organic compound and may or may not require all three lab periods. In order to complete the labs in the allotted time, you must be familiar with the lab procedure before the start of the lab period. Read the complete experiment and associated operations sections before coming to lab. There are no prelab questions, yet you are expected to understand what you will be doing in lab. It will be obvious if you are not prepared. For the last two labs, keep in mind that the results of one week will be used during subsequent weeks. Therefore, it is important that you understand what you are doing at each step and why you are doing it. An error in step 4 of a 6 step procedure means that the previous 4 steps, no matter how well they were done, are for naught. If you are in doubt about what to do, ask, and remember that old lab axiom, “Never throw anything away.”

Lab attendance/absences: Attendance is mandatory, and remember, “Don’t be on time, be early!”

Tardiness will result in loss of points (every 5 min late equals 2 pts) and you may miss important last minute instructions for the experiment. You will work with a partner for some experiments, make sure it is a team effort. If you do miss a lab, make sure that you talk to me to find out what you missed. THERE ARE NO MAKEUP LABS. If you have an approved reason for missing a lab see me by Friday January 16th. Lab Notebook: It is imperative that you maintain a complete notebook. This note book is to be separate from the lab report sheets. Anyone should be able to take your notebook and understand what was done, what results were obtained, and repeat the experiment. Write in the lab notebook with ballpoint pen, crossing through errors. Do not remove original pages from the notebook. I will collect the duplicate pages when you turn in your lab report. The lab notebook is to contain:

  1. Your name, course name, and section number on the cover.
  2. A table of contents on the first few pages.
  3. All your data, calculations, last minute modifications to the protocols, graphs, results, and conclusions must be in the notebook. Do not use scraps of paper to record any of these items.
  4. Each page needs to show your name (and your partner's name), date, and experiment title.
  5. Results should describe the results obtained (i.e. raw data and all calculations used to obtain "processed" data, tables and rough graphs). Final graphs, to be turned in, should be done on either a computer or with 10 mm x 10 mm graph paper.
  6. A general outline of :Introduction, Material and Methods, Data and Results, and Discussion should be followed. Safety: 1. Safety goggles or glasses must be worn at all times!!
    1. Appropriate dress is required including protective apron or coat.
    2. Report all injuries to me.
    3. No smoking, eating, or drinking in the laboratory.
    4. All chemicals, sharps, etc. must be disposed of properly. If you are not sure, ask.
    5. Women who are pregnant need to discuss the course with me because of potential and known mutagenic and teratogenic chemicals involved in some experiments.
    6. Come to lab prepared! Clean-up: At the end of the lab period, all reusable labware needs to be cleaned, rinsed with dH 2 O and allowed to dry. All equipment should be returned to their designated location. Water: We will be using lots of purified H 2 O this semester. In general you should always use distilled water except for external cooling baths. Assignments to be turned in: Lab assignments will consist of the following:
    7. The laboratory work sheets that will be posted on the course web site the week prior to a lab being preformed. You need to print these out before you come to lab. These need to be completely filled out and any assigned problems need to be completed.
    8. The lab notebook pages (including calculations, results, and any discussion) for that weeks lab will be stapled to the lab report sheet.
    9. If required, you may need to turn in your product at the end of lab or the beginning of the next lab. Make sure that you are turning in the compound that you say you are. 4. If you do not hand in assignments at the beginning of the lab, it is late and it will be assessed a late penalty. Late labs after one week will not be graded and recorded as a zero.
  • I retain the right to change this syllabus, as I deem necessary at any time during the semester. One final note: I have been in the lab long enough to know that things do not always go as planned when performing an experiment (i.e. you drop the test tube containing your precious sample, etc.). I will allow for unforeseeable error, however, if your errors are due to an obvious lack of preparation, leniency will not be forthcoming.